all-cis-1,3,5,7-tetrahydroxy-1,3,5,7-tetraphenylcyclotetrasiloxane | 6425-92-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: all-cis-1,3,5,7-tetrahydroxy-1,3,5,7-tetraphenylcyclotetrasiloxane
• 英文别名: cis-(1,3,5,7-tetrahydroxy)-1,3,5,7-tetraphenylcyclooctasiloxane；cis-1,3,5,7-tetrahydroxy-1,3,5,7-tetraphenylcyclotetrasiloxane；cis-2,4,6,8-tetrahydroxy-2,4,6,8-tetraphenylcyclotetrasiloxane；r-1,c-3,c-5,c-7-tetrahydroxytetraphenylcyclotetrasiloxane；cis-2,4,6,8-tetraphenyl-2,4,6,8-cyclotetrasiloxanetetrol；tetrahydroxy(tetraphenyl)cyclotetrasiloxane
• CAS: 6425-92-9
• 化学式: C₂₄H₂₄O₈Si₄
• 分子量: 552.792
• InChiKey: FTCGRHVDXDCFHR-VKAPFSNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.58
• 重原子数：
  36.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  117.84
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  all-cis-1,3,5,7-tetrahydroxy-1,3,5,7-tetraphenylcyclotetrasiloxane 在 三(五氟苯基)硼烷 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 C₅₆H₆₄O₁₂Si₈
  参考文献：
  名称：

  Janus环硅氧烷：扩展的Janus环和三环梯形硅氧烷的通用前体

  摘要：

  由全顺式-环四硅氧烷四醇或环四硅氧烷甲硅烷醇钠容易地制备全顺式-四甲硅烷氧基环四硅氧烷（Janus环硅氧烷）。此外，我们通过使用Janus环硅氧烷作为前体的Piers-Rubinsztajn反应证明了扩展的Janus环[RSi（OR'）O] 4的合成，该环含有各种官能团。值得注意的是，我们发现了意外的全顺式三环梯形硅氧烷作为副产物的形成。这些合成的化合物可能是定义明确的笼型倍半硅氧烷，Janus型纳米材料和多孔材料的潜在单体。

  DOI：

  10.1039/d0dt03045g
• 作为产物：
  描述：

  sodium tetraphenyl cyclotetrasiloxanolate 在 盐酸 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 以93.2%的产率得到all-cis-1,3,5,7-tetrahydroxy-1,3,5,7-tetraphenylcyclotetrasiloxane
  参考文献：
  名称：

  Synthesis of siloxane analogs of calixarenes

  摘要：

  以立体配位的顺式四苯基环四硅氧烷乙醇为基础，首次合成了钙烯烃的硅氧烷类似物。研究人员采用了不同的方法来研究新化合物的性质及其在水气界面上的行为。

  DOI：

  10.1007/s11172-015-1022-3

文献信息

• Synthesis of new stereoregular 2,4,6,8-tetraphenylcyclotetrasiloxanes with mesogenic groups and the influence of spatial isomerism on the phase state of individual isomers and their mixtures
  作者：N. N. Makarova、I. M. Petrova、P. V. Petrovskii、A. V. Kaznacheev、L. M. Volkova、M. A. Shcherbina、N. P. Bessonova、S. N. Chvalun、Yu. K. Godovskii

  DOI：10.1007/s11172-005-0059-0

  日期：2004.9

  The hydrosilylation of four isomers of tetra(dimethylsiloxy)tetraphenylcyclotetrasiloxane with (4′-cyanobiphenyl-4-yl)undec-10-enoate in the presence of a platinum catalyst afforded four liquid-crystalline stereoisomers of phenylcyclotetrasiloxane with mesogenic cyanobiphenyl groups. The reaction was performed for the first time. The influence of the spatial structure of the stereoisomers of tetraphenylcyclotetrasiloxanes with mesogenic groups on the formation of the liquid-crystalline state by thermooptical, X-ray diffraction, and calorimetric methods. The temperatures and enthalpies of phase transitions were determined, and their reversibility was shown. Differences in both the textures of melts formed on cooling and the phase state and in interplanar distances were found by optical microscopy and X-ray diffraction methods. Based on these data, the spatial structure of the isomers was concluded to affect the phase composition and type of packing in the liquid-crystalline state.

  在铂催化剂存在下，用(4′-氰基联苯-4-基)十一-10-烯酸酯对四(二甲基硅氧基)四苯基环四硅氧烷的四种异构体进行氢硅烷化反应，得到了四种带有中生氰基联苯基团的苯基环四硅氧烷液晶立体异构体。该反应是首次进行。通过热光学、X 射线衍射和量热法研究了带有介源基团的四苯基环四硅氧烷立体异构体的空间结构对液晶态形成的影响。确定了相变的温度和焓，并显示了其可逆性。通过光学显微镜和 X 射线衍射方法发现了冷却时形成的熔体质地和相态以及平面间距离的差异。根据这些数据，得出了异构体的空间结构会影响液晶态的相组成和堆积类型的结论。
• Facile Synthesis of Cyclic Fluorosiloxanes
  作者：Naoki Oguri、Nobuhiro Takeda、Masafumi Unno

  DOI：10.1246/cl.150692

  日期：2015.11.5

  Novel 1,3,5,7-tetrafluorocyclotetrasiloxanes were synthesized from cyclotetrasiloxanetetraol by a facile synthetic method. By adjusting the amount of the fluorinating reagent, synthesis of a single isomer of 1,3,5,7-tetrafluorocyclotetrasiloxanes as well as the preparation of all four isomers were accomplished. The products are expected to serve as potential precursors to not only well-defined silsesquioxanes but also asymmetric cyclic siloxanes.

  采用简便的合成方法从环四硅四醇合成了新型的 1,3,5,7-四氟环四硅氧烷。通过调整氟化试剂的用量，合成了 1,3,5,7-四氟环四硅氧烷的单一异构体，并制备了所有四种异构体。预计这些产品不仅可以作为明确定义的硅倍半硅氧烷的潜在前体，还可以作为不对称环状硅氧烷的潜在前体。
• Synthesis and Properties of Phenylsilsesquioxanes with Ladder and Double-Decker Structures
  作者：Hisayuki Endo、Nobuhiro Takeda、Masafumi Unno

  DOI：10.1021/om500010y

  日期：2014.8.11

  A series of phenyl-substituted silsesquioxanes with ladder and double-decker structures were synthesized, and their structures were determined. Their spectral and physical properties were compared with those of the previously reported cage, cyclic, and acyclic silsesquioxanes. Comparison of the thermal properties clearly showed that the structures strongly affect the thermal stability.

  合成了一系列具有梯形和双层结构的苯基取代的倍半硅氧烷，并确定了它们的结构。将它们的光谱和物理性质与先前报道的笼，环状和无环倍半硅氧烷的光谱和物理性质进行了比较。热性能的比较清楚地表明，该结构强烈影响热稳定性。
• The Influence of HCl Concentration on the Rate of the Hydrolysis–Condensation Reaction of Phenyltrichlorosilane and the Yield of (Tetrahydroxy)(Tetraphenyl)Cyclotetrasiloxanes, Synthesis of All Its Geometrical Isomers and Thermal Self-Condensation of Them under “Pseudo”-Equilibrium Conditions
  作者：Irina M. Petrova、Yury I. Lyakhovetsky、Nikolai S. Ikonnikov、Nataliya N. Makarova

  DOI：10.3390/molecules26144383

  日期：——

  obtained in the case of a-naphtylSiCl3. All-cis-(tetrahydroxy)(tetraphenyl)cyclotetrasiloxane was treated in acetone with HCl to give the other three geometric isomers (cis-cis-trans-, cis-trans-, and all-trans-). The thermal self-condensation of these four isomers under “pseudo”-equilibrium conditions (under atmospheric pressure) was investigated in different solvents, in quartz or molybdenum glass flasks

  苯基三氯硅烷在水-丙酮溶液中的水解-缩合反应速率和产物产率显着取决于溶液中 HCl (C HCl ) 的浓度。反应的主要产物是全顺- (四羟基)(四苯基)环四硅氧烷。这是从类似反应的早期公布的结果不同米-tolylSiCl 3，米-ClPhSiCl 3，和一个-naphtylSiCl，在其中形成的其它类型的一些产品。例如，反式-1,1,3,3-四羟基-1,3-二-α-萘基二硅氧烷在a- naphtylSiCl的情况下得到3 . 全顺-（四羟基）（四苯基）环四硅氧烷在丙酮中用盐酸处理，得到其他三种几何异构体（顺-顺-反-、顺-反-和全-反-）。在“假”平衡条件下（在大气压下）这四种异构体的热自缩合在不同溶剂中，在石英或钼玻璃烧瓶中进行了研究。通过APCI-MS和29 Si NMR光谱监测产物的组成。结果表明，清一色顺-和顺式-顺式-反式在甲苯或苯甲醚-异构体大多得到笼状博士-T 8,10,12
• Synthesis, Structures, and Thermal Properties of Symmetric and Janus “Lantern Cage” Siloxanes
  作者：Taishi Uchida、Yasunobu Egawa、Takuto Adachi、Naoki Oguri、Masato Kobayashi、Takako Kudo、Nobuhiro Takeda、Masafumi Unno、Ryoji Tanaka

  DOI：10.1002/chem.201805200

  日期：2019.2.1

  Symmetric and asymmetric (Janus‐type) new “lantern cage” siloxanes (PhSiO1.5)4(Me2SiO)4(RSiO1.5)4 (R=Ph or iBu) were synthesized through reaction of all‐cis‐[PhSi(OSiMe2Br)O]4 with all‐cis‐[RSi(OH)O]4 (R=Ph or iBu). These precursors were obtained by facile two or three‐step reactions from commercially available compounds. The spectroscopic properties of the resulting products were fully characterized and

  对称和非对称（詹纳斯型）新的“灯笼笼”硅氧烷（PhSiO 1.5）4（ME 2的SiO）4（RSiO 1.5）4（R =苯基或我卜）通过清一色的反应合成顺式- [PHSI（ OSiMe 2 Br）O] 4和全顺式[[RSi（OH）O] 4（R = Ph或i卜）。这些前体是通过容易地从市售化合物进行的两步或三步反应获得的。充分表征了所得产物的光谱性质，它们显示出高的热稳定性和升华而没有分解。晶体结构清楚地表明，灯笼笼的内部空位体积比八苯基倍半硅氧烷（PhSiO 1.5）8大得多。灯笼笼的DFT计算表明其电子状态与八聚倍半硅氧烷的电子状态截然不同。这些结果表明，笼型硅氧烷在分子中具有特征性的“场”。